4-Toluenesulfonyl chloride → HCID 59473789, compound

HRID 2069730Notes

Reaction equation

HRID 2069730 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([NH:13][CH2:14][CH2:15][OH:16])=S)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[O:16][CH2:15][CH2:14][N:13]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 59473782HCID 59473782, compound

Product 1

HCID 59473789HCID 59473789, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-3-(2-hydroxy-ethyl)-thiourea (306 mg, 1 mmol) in tetrahydrofuran (8 mL) was added aqueous 2N sodium hydroxide (1.25 mL, 2.5 mmol). With vigorous stirring a solution of para-toluene sulfonyl chloride (210 mg, 1.1 mmol) in tetrahydrofuran (4 mL) was added via drop-wise addition over 2 minutes. The material was stirred for 1 hour and then the solvent and volatiles were removed on the rotary evaporator. The remainder was taken up in ethyl acetate (25 mL) and water (15 mL) and shaken in a separatory funnel. The organic phase was collected and the aqueous phase was back extracted with ethyl acetate (2×20 mL). The organic phases were combined, dried over magnesium sulfate, filtered and stripped. The crude was purifed by preparative TLC, eluted with 7% methanol in methylene chloride to provide the desired product as a light green-grey solid (243 mg). (M+H)+=272/274 m/e.

Workup

  1. additionwas added via drop-wise addition over 2 minutes
  2. customthe solvent and volatiles were removed on the rotary evaporator
  3. stirringwater (15 mL) and shaken in a separatory funnel
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was back extracted with ethyl acetate (2×20 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. washeluted with 7% methanol in methylene chloride

Sources & evidence

ORD record
ord-61ea16f2d27d4635a20f5acb04f2b813
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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